CA2517141C - Method to produce a solid form of heparin - Google Patents
Method to produce a solid form of heparin Download PDFInfo
- Publication number
- CA2517141C CA2517141C CA002517141A CA2517141A CA2517141C CA 2517141 C CA2517141 C CA 2517141C CA 002517141 A CA002517141 A CA 002517141A CA 2517141 A CA2517141 A CA 2517141A CA 2517141 C CA2517141 C CA 2517141C
- Authority
- CA
- Canada
- Prior art keywords
- heparin
- solid form
- solution
- drum dryer
- drum
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920000669 heparin Polymers 0.000 title claims abstract description 100
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 229960002897 heparin Drugs 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000007787 solid Substances 0.000 title claims abstract description 29
- 238000001035 drying Methods 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 claims description 11
- 229960001008 heparin sodium Drugs 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- -1 tertiary amine salt Chemical class 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000356 contaminant Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 229920000045 Dermatan sulfate Polymers 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 description 4
- 229940051593 dermatan sulfate Drugs 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000012527 feed solution Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940018872 dalteparin sodium Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229940087051 fragmin Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000003055 low molecular weight heparin Substances 0.000 description 1
- 229940127215 low-molecular weight heparin Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/10—Heparin; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/727—Heparin; Heparan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/14—Powdering or granulating by precipitation from solutions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/10—Heparin; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45270103P | 2003-03-07 | 2003-03-07 | |
| US60/452,701 | 2003-03-07 | ||
| PCT/IB2004/000625 WO2004078791A1 (en) | 2003-03-07 | 2004-03-04 | Method to produce a solid form of heparin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2517141A1 CA2517141A1 (en) | 2004-09-16 |
| CA2517141C true CA2517141C (en) | 2008-11-18 |
Family
ID=32962743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002517141A Expired - Fee Related CA2517141C (en) | 2003-03-07 | 2004-03-04 | Method to produce a solid form of heparin |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6933372B2 (enExample) |
| EP (1) | EP1611161B1 (enExample) |
| JP (1) | JP2006519906A (enExample) |
| AR (1) | AR043731A1 (enExample) |
| AT (1) | ATE368057T1 (enExample) |
| CA (1) | CA2517141C (enExample) |
| CL (1) | CL2004000414A1 (enExample) |
| DE (1) | DE602004007784T2 (enExample) |
| ES (1) | ES2289492T3 (enExample) |
| MX (1) | MXPA05009498A (enExample) |
| TW (1) | TWI274761B (enExample) |
| WO (1) | WO2004078791A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0327723D0 (en) * | 2003-09-15 | 2003-12-31 | Vectura Ltd | Pharmaceutical compositions |
| CN101575385B (zh) * | 2008-05-09 | 2011-01-12 | 青岛九龙生物医药有限公司 | 萃取法分离肝素钠中的多硫酸软骨素的方法 |
| CN101831008B (zh) * | 2009-03-11 | 2013-04-10 | 四川茂森生物科技有限公司 | 粗品肝素钠精制生产新工艺 |
| CN108508129B (zh) * | 2018-04-03 | 2020-11-27 | 青岛海洋生物医药研究院股份有限公司 | 一种肝素类药物生物效价的测定方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2034599A (en) | 1933-07-10 | 1936-03-17 | Buffalo Foundry & Machine Co | Method of drying inorganic salts and sludges |
| US2571679A (en) | 1948-07-08 | 1951-10-16 | Carlo Erba S A | Process for preparing purified heparin |
| US2797184A (en) | 1953-07-01 | 1957-06-25 | Upjohn Co | Process for the recovery of heparin |
| US2884358A (en) | 1957-04-22 | 1959-04-28 | Southern California Gland Co | Process for preparing crude heparin |
| US2954321A (en) | 1957-09-23 | 1960-09-27 | Upjohn Co | Process for preparing heparin |
| US3337409A (en) | 1963-11-20 | 1967-08-22 | Rexall Drug Chemical | Process for the recovery of heparin |
| US3330327A (en) * | 1964-03-30 | 1967-07-11 | Continental Oil Co | Drying tertiary amine oxides on extended heated surfaces at elevated temperatures |
| US3817831A (en) | 1973-01-10 | 1974-06-18 | Wilson Pharm & Chem Corp | Process for production of alkali metal salt of heparin |
| CA1136620A (en) | 1979-01-08 | 1982-11-30 | Ulf P.F. Lindahl | Heparin fragments having selective anticoagulation activity |
| US4510135A (en) * | 1982-04-21 | 1985-04-09 | Research Corporation | Orally administered heparin |
| DE3422518A1 (de) * | 1984-06-16 | 1985-12-19 | B. Braun Melsungen Ag, 3508 Melsungen | Heparin-derivate, verfahren zu ihrer herstellung, diese enthaltende arzneimittel und ihre verwendung bei der behandlung von fettstoffwechselstoerungen |
| DK170015B1 (da) * | 1992-03-19 | 1995-05-01 | Sudurnesja Hitaveita | Saltprodukt samt fremgangsmåde til dets fremstilling |
| US5668118A (en) * | 1992-07-24 | 1997-09-16 | Cavalier Pharmaceuticals | Method of synthesis of 2-O-desulfated Heparin and use thereof for inhibition of elastase and Cathepspin G |
| DE4310088A1 (de) | 1993-03-27 | 1994-09-29 | Hoechst Ag | Verfahren zur Herstellung und Aufarbeitung von in wäßrigem Medium löslichen N-Hydroxyalkylchitosanen |
| AU682792B2 (en) * | 1994-10-13 | 1997-10-16 | Cv Therapeutics, Inc. | Method of manufacturing non-absorbable synthetic sulfated polysaccharides |
| CA2173642C (en) * | 1995-04-10 | 1999-11-02 | James Vincent Gruber | Process for derivatizing polyglucosamines |
| TR200000086T2 (tr) | 1997-07-16 | 2000-08-21 | Akzo Nobel N.V. | Heparin üretimi için işlem. |
| CN1218058A (zh) | 1997-11-26 | 1999-06-02 | 中国林业科学研究院林产化学工业研究所 | 肝素的喷雾干燥方法 |
| US6485945B1 (en) | 1999-02-17 | 2002-11-26 | Nurture, Inc. | Polysaccharide compositions and uses thereof |
| AU3623601A (en) | 2000-02-07 | 2001-08-14 | Granate Seed Ltd | Process for extraction of beta-glucan from cereals and products obtained therefrom |
-
2004
- 2004-02-27 US US10/789,466 patent/US6933372B2/en not_active Expired - Fee Related
- 2004-03-02 CL CL200400414A patent/CL2004000414A1/es unknown
- 2004-03-04 EP EP04717174A patent/EP1611161B1/en not_active Expired - Lifetime
- 2004-03-04 ES ES04717174T patent/ES2289492T3/es not_active Expired - Lifetime
- 2004-03-04 CA CA002517141A patent/CA2517141C/en not_active Expired - Fee Related
- 2004-03-04 JP JP2006506297A patent/JP2006519906A/ja not_active Ceased
- 2004-03-04 WO PCT/IB2004/000625 patent/WO2004078791A1/en not_active Ceased
- 2004-03-04 DE DE602004007784T patent/DE602004007784T2/de not_active Expired - Lifetime
- 2004-03-04 MX MXPA05009498A patent/MXPA05009498A/es active IP Right Grant
- 2004-03-04 AT AT04717174T patent/ATE368057T1/de not_active IP Right Cessation
- 2004-03-05 TW TW093105873A patent/TWI274761B/zh not_active IP Right Cessation
- 2004-03-05 AR ARP040100707A patent/AR043731A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TWI274761B (en) | 2007-03-01 |
| EP1611161B1 (en) | 2007-07-25 |
| ATE368057T1 (de) | 2007-08-15 |
| US20040176581A1 (en) | 2004-09-09 |
| ES2289492T3 (es) | 2008-02-01 |
| DE602004007784T2 (de) | 2007-12-06 |
| EP1611161A1 (en) | 2006-01-04 |
| US6933372B2 (en) | 2005-08-23 |
| MXPA05009498A (es) | 2005-10-18 |
| WO2004078791A1 (en) | 2004-09-16 |
| TW200502255A (en) | 2005-01-16 |
| CL2004000414A1 (es) | 2005-02-04 |
| JP2006519906A (ja) | 2006-08-31 |
| AR043731A1 (es) | 2005-08-10 |
| CA2517141A1 (en) | 2004-09-16 |
| DE602004007784D1 (de) | 2007-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130304 |